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High-selectivity mercury ion near-infrared fluorescence probe taking phenyl thionocarbonate as recognition receptor

A technology based on ester groups and hydrogen atoms, which is applied in the field of mercury ion near-infrared fluorescent probes, can solve the problems of harsh reaction conditions, complex synthesis steps, and poor photostability, and achieve simple synthesis, convenient detection and operation, and good stability.

Inactive Publication Date: 2017-03-29
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported fluorescent probes have defects such as low quantum efficiency, poor photostability, complex synthesis steps, strong influence of pH changes, harsh reaction conditions, and difficult detection methods.

Method used

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  • High-selectivity mercury ion near-infrared fluorescence probe taking phenyl thionocarbonate as recognition receptor
  • High-selectivity mercury ion near-infrared fluorescence probe taking phenyl thionocarbonate as recognition receptor
  • High-selectivity mercury ion near-infrared fluorescence probe taking phenyl thionocarbonate as recognition receptor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] (Scheme 1) Dissolve 500 mg (1.49 mmol) of fluorescent dye, 516 mg (2.98 mmol) of phenyl thiochloroformate (384 mg, 2.98 mmol) and N,N-diisopropylethylamine (DIPEA) in 15 mL of dichloromethane , then stirred and reacted at 25°C for 9h, and then rotary evaporated to obtain the crude product, and finally used dichloromethane:methanol=60:1 system for column chromatography to obtain 647mg of pure product with a yield of 92%.

[0038](Scheme 2) Dissolve 500 mg (1.49 mmol) of fluorescent dye, 540 mg (3.13 mmol) of phenyl thiochloroformate (384 mg, 2.98 mmol) and N,N-diisopropylethylamine (DIPEA) in 15 mL of dichloromethane , then stirred and reacted at 25°C for 9h, and then rotary evaporated to obtain the crude product, and finally used dichloromethane:methanol=60:1 system for column chromatography to obtain 645mg of pure product with a yield of 92%.

[0039] (Scheme 3) Dissolve 500 mg (1.49 mmol) of fluorescent dye, 257 mg (1.49 mmol) of phenyl thiochloroformate (...

Embodiment 2

[0043] Different concentrations of Hg 2+ (0-10μM) on the fluorescence spectrum of the probe (5μM). The above determinations were carried out in an aqueous solution of 5 mM HEPES, pH 7.0, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25° C. for 20 min. See results figure 1 .

[0044] From figure 1 It can be seen that with the Hg in the probe solution 2+ As the concentration increases, the fluorescence intensity gradually increases, and at 0-10μM Hg 2+ Concentration range, Hg 2+ The concentration and fluorescence intensity showed a linear relationship. Therefore, the probe of the present invention can more accurately determine the content of mercury ions in the sample to be tested.

Embodiment 3

[0046] Fig. 2(a) Effect of different analytes on the fluorescence spectrum of the probe (5 μM). (b) Quantitative analysis of Hg with different analyte pair probes (5 μM) by fluorescence spectrometry 2+ (6μM). Analytes include: Potassium ion K + , Sodium ion Na + , calcium ion Ca 2+ , Magnesium ion Mg 2+ , ferrous ion Fe 2+ , iron ion Fe 3+ , aluminum ion Al 3+ , silver ion Ag + , copper ion Cu 2+ , Cadmium ion Cd 2+ , lead ion Pb 2 + , Zinc ion Zn 2+ , fluoride ion F - , nitrate ion NO 3 - , nitrite ion NO 2 - , Carbonate CO 3 2- , bicarbonate HCO 3 - , Chloride ion Cl - , Sulfate ion SO 4 2- , sulfite ion SO 3 2- , bisulfite ion HSO 3 - , Bromide Br - , and their concentration is 50 μM. All test conditions are carried out in 5mM HEPES, pH 7.0 aqueous solution, the probe used is the probe prepared in Example 1, and all spectral tests are measured after acting at 25°C for 20 minutes. The results are shown in Figure 2(a) and (b). Specifically, pip...

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Abstract

The invention relates to a high-selectivity mercury ion near-infrared fluorescence probe taking phenyl thionocarbonate as a recognition receptor, and more specifically relates to a phenyl thionocarbonate compound which can be applied in detection of mercury ions as a mercury ion fluorescence probe. The high-selectivity mercury ion near-infrared fluorescence probe comprises at least one of the following functions: high selectivity identification of mercury ions can be realized, sensitive response on mercury ions can be realized, rapid detection of mercury ions can be realized, performance is stable, long term storage can be realized, it is beneficial for detection of mercury ions in practical samples, and relatively high capacity of resisting disturbance is achieved.

Description

technical field [0001] The invention relates to a mercury ion near-infrared fluorescent probe using thiophenylcarbonate as a recognition acceptor, which can be used in high-selective recognition of mercury ions under specific conditions, or can measure the concentration of mercury ions in a sample. Background technique [0002] Mercury has been a global pollutant of concern. Mercury exists in the environment as inorganic mercury and organic mercury (mainly in the form of methylmercury). Mercury's high toxicity, bioaccumulation and refractory properties make people talk about mercury. In addition, inorganic mercury can be transformed into more toxic organic mercury in the aquatic biological system, and finally accumulate in the human body through the food chain. This is the Minamata disease event that occurred in Japan in the 1950s. Studies have shown that the harm of mercury to the human body mainly involves the central nervous system, digestive system and kidneys, and als...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/34C09K11/06G01N21/64
CPCC07D265/34C09K11/06C09K2211/1007C09K2211/1033G01N21/6428G01N21/643
Inventor 王雅伟张萌吴柳柳彩云段庆霞王作凯朱宝存
Owner UNIV OF JINAN
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